For the issue of giving to the local church, we have to look to Paul because, as you say, Jesus was dealing with a pre-local church context. In fact, he was dealing with a Jewish context where tithing was a part of Torah, and he encouraged the people to tithe. "You should have practiced the latter, without neglecting the former." (Mt. 23:23)
So then, to Paul. This is from 1 Corinthians 9.
1 Am I not free? Am I not an apostle? Have I not seen Jesus our Lord? Are you not the result of my work in the Lord? 2 Even though I may not be an apostle to others, surely I am to you! For you are the seal of my apostleship in the Lord.
3 This is my defense to those who sit in judgment on me. 4 Don’t we have the right to food and drink? 5 Don’t we have the right to take a believing wife along with us, as do the other apostles and the Lord’s brothers and Cephas? 6 Or is it only I and Barnabas who lack the right to not work for a living?
7 Who serves as a soldier at his own expense? Who plants a vineyard and does not eat its grapes? Who tends a flock and does not drink the milk? 8 Do I say this merely on human authority? Doesn’t the Law say the same thing? 9 For it is written in the Law of Moses: “Do not muzzle an ox while it is treading out the grain.” Is it about oxen that God is concerned? 10 Surely he says this for us, doesn’t he? Yes, this was written for us, because whoever plows and threshes should be able to do so in the hope of sharing in the harvest. 11 If we have sown spiritual seed among you, is it too much if we reap a material harvest from you? 12 If others have this right of support from you, shouldn’t we have it all the more?
But we did not use this right. On the contrary, we put up with anything rather than hinder the gospel of Christ.
13 Don’t you know that those who serve in the temple get their food from the temple, and that those who serve at the altar share in what is offered on the altar? 14 In the same way, the Lord has commanded that those who preach the gospel should receive their living from the gospel.
15 But I have not used any of these rights. And I am not writing this in the hope that you will do such things for me, for I would rather die than allow anyone to deprive me of this boast. 16 For when I preach the gospel, I cannot boast, since I am compelled to preach. Woe to me if I do not preach the gospel! 17 If I preach voluntarily, I have a reward; if not voluntarily, I am simply discharging the trust committed to me. 18 What then is my reward? Just this: that in preaching the gospel I may offer it free of charge, and so not make full use of my rights as a preacher of the gospel.
Verse 14 is crucial because Paul declares a command directly from Jesus, that those who preach the gospel should receive their living from the gospel. Paul, however, lets the Corinthians off the hook in this regard, not because he's being magnanimous, but because of their stubborn and judgmental hearts (v. 3).
The problem is not that Paul shouldn't be asking for money and is, it's that the congregation is judgmental toward and offended by him when he does. The root of this problem, as I stated in the previous post, is that money is an idol for all of us.
Let me go one step further. Almost every pastor I know would do the ministry for free if it were possible. I can't think of a single person in the ministry, that I know personally, who is doing this because it seemed like a wise career choice. They are all doing it because they believe God has called them to the task, and they are so passionate about the proclamation of the Gospel that they would forsake lucrative careers in other fields to give their whole lives to the mission of Jesus. (In case you were wondering, a Master of Divinity is the only Master degree where the typical holder earns less than those with just a Bachelor degree.)
Nobody goes into ministry for the money. I, myself, ministered for free for 2 years. I'm trying very hard to minister for free right now, and am extremely grateful for the generosity of Ember Church in the meantime. Paul ministered for free because the people in Corinth were hard-hearted and judgmental. (In fact, it's more likely that he had to rely on the support of other, more generous and kingdom-minded churches to supplement what he lacked from his tent-making work.) But that is not God's plan for those who preach the gospel. Again, verse 14, "The Lord [Jesus] has commanded that those who preach the gospel should receive their living from the gospel."
We could even drop down another level and talk about what Jesus commanded his disciples when he sent them out in, say, Mark 6. (Which is the passage I'm preaching from this week at Ember.) Verse 8, "Take nothing for the journey except a staff--no bread, no bag, no money in your belts." What is he saying? He's saying, "Trust my Father to provide for your needs through the generosity of those to whom you preach." So even as far back as the first commissioning of the disciples we see that Jesus' intention is for them to "receive their living from the Gospel."
Someone might say, "Well that's convenient for you to say, guilting people into giving so that you can earn a salary." But that cynicism doesn't negate the explicit command of Jesus. While we pastors, Paul included, might walk on eggshells and put up with a lot because of this cynicism and judgmentalism, it is not what Jesus intends for his church. And the cynicism is wrong. It is, biblically, wrong. But we pastors, like Paul, put up with it for the sake of the gospel. We hem and we haw over money, and we pussyfoot around because we think that, because we earn our living by preaching, we don't have the moral authority to preach on money. That's simply bogus. If money is a near-universal idol, and the Gospel has something to say about all of our idols, and we're called to preach the Gospel, then we've got a moral obligation and a command from Jesus himself to preach on money. If you (and this is a general you) as a Christian are offended by biblical teaching on money, then your idol is showing, and you should expect God to do something to your idol along the lines of what he did to Shiloh, and then to the Temple in Jerusalem.